The Journal of organic chemistry

Regio-and Diastereoselective Allenylation of Aldehydes in Aqueous Media: Total Synthesis of (+)-Goniofufurone1

XH Yi, Y Meng, XG Hua, CJ Li

Index: Yi, Xiang-Hui; Meng, Yue; Hua, Xiao-Gang; Li, Chao-Jun Journal of Organic Chemistry, 1998 , vol. 63, # 21 p. 7472 - 7480

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Citation Number: 97

Abstract

The regio-and diastereoselectivities of metal-mediated allenylation of carbonyl compounds were investigated in aqueous media. Different metal mediators showed varied regioselectivities on product formation during propargylation-allenylation reactions of carbonyl compounds with simple propargyl bromide. Under the standard reaction conditions, the use of indium provided the highest regioselectivity, with a preference of ...

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Iodobenzene Structure

591-50-4

Iodobenzene

~%

(3-Bromo-1-propynyl)benzene solution Structure

1794-48-5

(3-Bromo-1-prop...

2-Hexyn-1-ol Structure

764-60-3

2-Hexyn-1-ol

Methanesulfonyl chloride Structure

124-63-0

Methanesulfonyl...

~80%

hex-2-yn-1-ol,methanesulfonic acid Structure

104506-68-5

hex-2-yn-1-ol,m...

Pent-1-yne Structure

627-19-0

Pent-1-yne

~%

hex-2-yn-1-ol,methanesulfonic acid Structure

104506-68-5

hex-2-yn-1-ol,m...

Methyl 2-hexynoate Structure

18937-79-6

Methyl 2-hexynoate

~%

hex-2-yn-1-ol,methanesulfonic acid Structure

104506-68-5

hex-2-yn-1-ol,m...

Heptanal Structure

111-71-7

Heptanal

3-Bromopropyne Structure

106-96-7

3-Bromopropyne

~%

1-(2-Propynyl)heptane-1-ol Structure

27907-00-2

1-(2-Propynyl)h...

dec-2-en-4-one Structure

63024-86-2

dec-2-en-4-one

Heptanal Structure

111-71-7

Heptanal

3-Bromopropyne Structure

106-96-7

3-Bromopropyne

~%

1-(2-Propynyl)heptane-1-ol Structure

27907-00-2

1-(2-Propynyl)h...

dec-2-en-4-one Structure

63024-86-2

dec-2-en-4-one

2-BUTENE-1,4-DIOL Structure

821-11-4

2-BUTENE-1,4-DIOL

~58%

Glycolaldehyde Structure

141-46-8

Glycolaldehyde

Benzaldehyde Structure

100-52-7

Benzaldehyde

3-Bromopropyne Structure

106-96-7

3-Bromopropyne

~%

3-methyl-5-phenyl-2(5H)-furanone Structure

104516-09-8

3-methyl-5-phen...

1-PHENYL-3-BUTYN-1-OL Structure

1743-36-8

1-PHENYL-3-BUTY...

hex-2-yn-1-ol,methanesulfonic acid Structure

104506-68-5

hex-2-yn-1-ol,m...

~46%

1-Bromo-2-Hexyne Structure

18495-25-5

1-Bromo-2-Hexyne

Methyl 2-hexynoate Structure

18937-79-6

Methyl 2-hexynoate

~%

1-Bromo-2-Hexyne Structure

18495-25-5

1-Bromo-2-Hexyne


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